Mistress Kristy and Jack, her new sissy (1)

Kristy had been on dating apps for months, and despite being relatively inexperienced, she had managed to attract quite a few suitors. They were all men who seemed to be infatuated with her, men who couldn’t help but fawn over her every word and action. But despite their admiration, none of them had ever gone beyond the initial stages of dating. They were content with being friends, or maybe even casual acquaintances, but never anything more. It was as if there was an invisible barrier that kept them from crossing the line into anything truly meaningful.

And then, one day, she came across a message that would change everything. A new potential match had appeared on her screen, and the message he had sent was nothing short of intriguing.

“Hello there, Kristy,” it read. “My name is Jack, and I’m a sissy, pervert, and have been in chastity for several months. I’ve been looking for a mistress who can take control of me and do whatever she wishes. I’ve heard a lot about you, and I think you might be just what I’m looking for.”

Kristy, really fascinated by Jack being a sissy

The message was short, but it spoke volumes. Kristy was fascinated by Jack’s confession, and she couldn’t help but wonder what it would be like to have such a unique and intriguing partner. She quickly responded, expressing her interest in meeting him and learning more about his desires. As they exchanged messages, she found herself becoming increasingly drawn to the idea of being the one in control, of being Jack’s mistress and guiding him through this new world of sexual exploration.

But there was one thing that bothered her. Jack had mentioned being in chastity, and while she had heard of chastity devices before, she wasn’t entirely sure what they entailed. So, she decided to do some research.

After spending several hours online, she learned that sissies were men who were often controlled by a mistress and wore chastity devices, which prevented their penises from becoming erect. They could still be aroused, however, and their pleasure could be derived from other means, such as prostate stimulation. The devices were designed to keep them in a state of perpetual arousal, with their desires constantly teetering on the brink of satisfaction but never quite being fulfilled.

Kristy found this concept both fascinating and empowering. It seemed like the perfect arrangement for someone like her, someone who craved control and dominance in the bedroom.

First meeting with Jack, the pervert sissy

She was eager to meet Jack and take control of his key, to see firsthand what it was like to have a submissive sissy partner who would do whatever she wanted, whenever she wanted. The thought of exploring this new world of sexual dominance and power play was intoxicating, and she couldn’t wait to dive in headfirst.

As they continued to exchange messages, they arranged to meet at a discreet location, somewhere private where they could discuss their desires openly without fear of judgment. Kristy couldn’t help but feel a mix of nervousness and anticipation as she prepared for the meeting. She wore her most alluring lingerie, something that would accentuate her curves and leave no doubt in Jack’s mind about her intentions.

She wanted to make sure that he knew she was in control from the moment they met. When Jack finally arrived, Kristy could tell immediately that he was every bit as intriguing as his messages had led her to believe. His chastity device was visible beneath his clothes, a constant reminder of his submission and arousal. As they exchanged greetings, she took him by the hand and led him to a secluded corner of the room.

There, she sat down on a couch, her legs spread invitingly and motioned for him to sit beside her. The power dynamic between them was palpable, and it was clear that Jack was eager to please her.

Kristy, taking control of Jack

Without further ado, Kristy reached over and began to undo the buttons of Jack’s shirt. She reveled in the feel of his skin beneath her fingers as she peeled away each layer, exposing him more and more. When his chest was finally bared, she let out a soft laugh, noticing that he was wearing a lacy black thong. Then, she reached down and tugged at it, pulling it aside to reveal his hard, trapped cock.

“Oh, Jack,” she purred, fondling his balls through the chastity device. “You’ve been such a naughty boy.”

She squeezed his balls roughly, eliciting a gasp from him.

“I think it’s time I taught you a lesson.”

She leaned in close, her breath hot against his ear.

“Do you know what I want to do to you?” she whispered, her fingers still working his cock and balls.

As Jack nodded eagerly, his face flushed with arousal, Kristy grinned wickedly.

“I want to make you beg for it,” she hissed. “I want you to beg me to fuck you up the ass.”

She reached around and grabbed his chin, forcing him to look her in the eye.

“Do you understand?”

Jack’s mouth went dry, and his heart raced. He nodded slowly, his gaze never leaving hers.

“Yes, Mistress,” he managed to croak. “I understand.”

Kristy smiled, her lips curling into a predatory grin.

“Good boy,” she purred, her fingers slipping lower to caress his trapped cock through the chastity device.
“But first,” she continued, “I think it’s time you showed me how much you want this.”

Poor Jack, really frustrated

She squeezed his balls one final time before pulling her hand away, leaving him aching for more. Jack let out a moan of frustration, his hips bucking forward instinctively.

“Please, Mistress,” he begged, his voice strained. “Please let me feel you inside me. I’ll do anything you want.”

Kristy leaned back, considering him for a moment before reaching down to tug at his lacy thong. In one swift motion, she yanked it aside, revealing his tight, puckered hole.

“Are you sure you’re ready for this, my little sissy boy?” she purred, her fingers teasing his entrance. “Because once I take you, there’s no going back.”

Jack nodded desperately, his body trembling with need.

“Yes, Mistress,” he whimpered. “I’m your little sissy boy.”

Kristy chuckled darkly, amused by his eagerness. She positioned herself between Jack’s spread legs and lined up her aching core with his entrance.

“Then take me,” she growled, pushing slowly inside him.

Jack let out a gasp as he felt her warm, wet flesh press against his virgin ass.

“Squeeze tight,” she ordered, feeling his muscles clench around her.

With a final thrust, she buried herself to the hilt inside him, hissing through her teeth as she felt him stretch and accommodate her. Jack cried out in pleasure, arching his back as he felt Kristy’s full weight press down on him.

“Oh, God,” he moaned, his eyes rolling back in his head.

“You feel so good, Mistress.”

Then, a very strong orgasm for the pervert sissy

He reached up, grasping at her hips, digging his nails into her skin as he rode out the sensation of being taken by her. Kristy let out a low, satisfied groan, her hips beginning to move rhythmically against Jack’s. She leaned forward, her breasts pressing against his back as she began to fuck him hard and fast.

“That’s it, my pretty little sissy,” she hissed in his ear. “Take it all, and take it well.”

Jack’s eyes fluttered shut, his head falling back against her shoulder as he surrendered to the sensation of being used by her.

He could feel the pressure building inside him, the familiar ache of impending orgasm beginning to coil in his belly.

“Cum for me, Jack,” Kristy whispered, her hips speeding up even more.

“Let go and cum all over my cock.”

Jack’s body shook with the force of his orgasm, his ass clenching tightly around her as he came, his hot seed spilling onto her chest.

“That’s a good boy,” she purred, collapsing forward to rest her weight against him.

“Now, it’s my turn.”

Nice and really exciting future for Mistress Kristy and her sissy

With a final thrust, she came as well, her body tensing around him as she emptied herself into his ass. As the wave of pleasure subsided, they lay there for a moment, catching their breath. Jack couldn’t help but feel a sense of awe and gratitude towards Kristy. He had never experienced anything like this before, and he couldn’t wait to explore further the world of sexual dominance and submission that she had opened up to him.

As he looked up at her, his eyes shining with a mixture of lust and adoration, he knew that this was only the beginning. Kristy smiled down at him, running a finger along his cheek.